Herbicidal heterocyclicmethylenebenzenesulfonamides

ABSTRACT

Novel benzenesulfonamide compounds containing an ortho-heterocyclicmethylene substituent such as N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide are useful as preemergent and/or postemergent herbicides and/or plant growth regulants.

Background of the Invention

European patent application (EP-A) No. 44,209, published Jan. 20, 1982discloses herbicidal compounds of formula ##STR1## where L may be CO₂R₁₀, CONR₃ R₄, CN, Cl, Br, NR₃ R₄, N⁺ R₃ R₄ R_(4'), N(R₄)C(O)R₅,N(R₄)C(O)NHR₆, N(R₄)C(O)OR₇, S(O)_(n) R₇, OR₉, SO₂ NR₃ R₄, OH, OC(O)R₁₁,OC(O)NHR₁₂ or OC(O)OR₁₃.

EP-A Nos. 83,975, published July 20, 1983, and 85,476, published Aug.10, 1983, disclose herbicidal compounds of formula ##STR2## where Q isvarious 5- and 6-membered unsaturated, saturated and partially saturatedheterocycles.

U.S. Pat. No. 4,370,480, issued Jan. 25, 1983, discloses herbicidalsulfonamides of formula ##STR3## where R₁ may be ##STR4## B is O orS(O)_(G).

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I, suitableagricultural compositions containing them and their method-of-use asgeneral and/or selective preemergence and/or postemergence herbicidesand/or plant growth regulants. ##STR5## wherein R is H or CH₃ ;

R₁ is H, F, Cl, Br, CH₃, CF₃, OCH₃, SCH₃, OCHF₂ or SCHF₂ ;

n is 1 or 2;

Q is ##STR6## R₅, R₆, R₇ and R₁₀ are independently H or CH₃ ; R₈ is H,CH₃, CH₂ CH₃, SH, SCH₃, SCH₂ CH₃, OCH₃, OCH₂ CH₃, SCF₂ H, SCH₂ CH═CH₂ orSCH₂ CN;

R₉ is H or Cl;

R₁₁ and R₁₂ are independently H, CH₃ or OCH₃ ; and

R₁₃ and R₁₄ are independently CH₃ or OCH₃ ; ##STR7## X is CH₃, OCH₃,OCH₂ CH₃, Cl, F, Br, I, OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃or CF₃ ;

Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, ##STR8## orcyclopropyl; m is 2 or 3;

L₁ and L₂ are independently O or S;

R₂ is H or CH₃ ;

R₃ and R₄ are independently C₁ -C₂ alkyl;

Z is CH or N;

Y₁ is O or CH₂ ;

X₁ is CH₃, OCH₃, OC₂ H₅ or OCF₂ H; and

Y₂ is H or CH₃ ; provided that

(a) when X is Cl, F, Br or I, then Z is CH and Y is OCH₃, OC₂ H₅,N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂ H;

(b) when X or Y is OCF₂ H, then Z is CH; and ##STR9## then A is A-4;

(d) when Q is Q-1, Q-2, Q-4, Q-5, Q-6, Q-8, Q-23, Q-24, Q-25, Q-26,Q-27, Q-28, Q-29, Q-45, Q-46, Q-47, Q-51, or Q-52 and A is A-1, then oneof R₅ or R₆ is other than H;

(e) when Q is Q-10 or Q-13 and A is A-1, then R₈ is other than H, CH₃ orCH₂ CH₃ ;

(f) when Q is Q-11, Q-12, Q-15 or Q-16, then A is A-2, A-3 or A-4;

(g) when Q is Q-14 and A is A-1, then R₉ is other than H;

(h) when Q is Q-3, Q-18 or Q-19 and A is A-1, then R₅ is CH₃ ;

(i) when Q is Q-31 or Q-33 and A is A-1, then one of R₅, R₆ or R₇ isother than H;

(j) when Q is Q-48 and A is A-1, then one of R₅, R₁₁ or R₁₂ is otherthan H;

(k) when Q is Q-49 or Q-50 and A is A-1, then one of R₁₁ or R₁₂ is otherthan H;

(l) when Q is Q-53 or Q-54 and A is A-1, then one of R₁₃ and R₁₄ isother than H; and their agriculturally suitable salts.

Preferred for reasons of greater ease of synthesis and/or greaterherbicidal efficacy are:

(1) Compounds of Formula I wherein R is H.

(2) Compounds of Preferred 1 where Q is Q-1, Q-2, Q-3, Q-6, Q-7, Q-8,Q-9, Q-10, Q-11, Q-12, Q-13, Q-14, Q-15, Q-17, Q-20, Q-23, Q-24, Q-25,Q-26, Q-29, Q-30, Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-40,Q-41, Q-43, Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53,Q-54.

(3) Compounds of Preferred 2 where A is A-1 and Y is CH₃, OCH₃, CH₂OCH₃, NHCH₃, CH₂ CH₃, CH(OCH₃)₂ or cyclopropyl.

(4) Compounds of Preferred 3 where R₁ is H, Cl, CH₃, SCH₃ or OCH₃ and Xis CH₃, OCH₃, Cl, Br or OCF₂ H.

(5) Compounds of Preferred 4 where n is 2.

(6) Compounds of Preferred 4 where Q is Q-1, Q-2 or Q-3.

(7) Compounds of Preferred 4 where Q is Q-6, Q-7, Q-8 or Q-9.

(8) Compounds of Preferred 4 where Q is Q-10, Q-11 or Q-12.

(9) Compounds of Preferred 4 where Q is Q-13, Q-14, Q-15, Q-17 or Q-20.

(10) Compounds of Preferred 4 where Q is Q-23, Q-24, Q-25, Q-26, Q-29 orQ-30.

(11) Compounds of Preferred 4 where Q is Q-31, Q-32, Q-33 or Q-34.

(12) Compounds of Preferred 4 where Q is Q-35, Q-36, Q-37 or Q-38.

(13) Compounds of Preferred 4 where Q is Q-40, Q-41, Q-43 or Q-44.

(14) Compounds of Preferred 4 where Q is Q-45, Q-46, Q-47, Q-48, Q-49,Q-50, Q-51, Q-52, Q-53 or Q-54.

An exemplary compound is:N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide,m.p. 171°-175° C.

Detailed Description of the Invention Synthesis

The compounds of Formula I can be prepared by one or more of the methodsdescribed below in Equations 1, 2 and 3.

As shown in Equation 1 below, the compounds of Formula I can be preparedby treating sulfonamides of Formula II with the methyl ester of apyrimidine or triazinecarbamic acid of Formula III in the prsence of anequimolar quantity of trimethylaluminum. ##STR10## wherein

A, R, R₁, Q and n are as previously defined.

The reaction of Equation 1 is best carried out at temperatures between23° to 83° C. in an inert solvent such as methylene chloride or1,2-dichloroethane for 12 to 96 hours under an inert atmosphere. Theproduct can be isolated by the addition of an aqueous acetic acidsolution followed by extraction of the product into methylene chlorideor direct filtration of a product of low solubility. The product canordinarily be purified by trituration with solvents such as n-butylchloride, ethyl acetate or diethyl ether or by chromatographyprocedures. The methyl carbamates, III, can be conveniently prepared bytreatment of the corresponding heterocyclic amines of Formula VI withdimethyl carbonate or methyl chloroformate in the presence of a basesuch as sodium hydride or pyridine.

Further details of this reaction and the preparation of the carbamatesof Formula III can be found in EP-A No. 83,975 (published July 20,1983).

Alternatively, compounds of Formula I can be prepared by the reaction ofsulfonamides of Formula II with the phenyl ester of the appropriatecarbamic acid, IV, in the presence of an equimolar quantity of atertiary amine base such as 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).##STR11## wherein

A and R are as previously defined.

The reaction of Equation 2 is best carried out at 20° to 30° C. in aninert solvent such as dioxane or acetonitrile. Aqueous acid work-upaffords the desired products, according to the teachings of EP-A No.70,804 (published Jan. 26, 1983) and South African patent applications825,042 and 830,441. The phenyl carbamates, IV, can be prepared bytreating the corresponding heterocyclic amines of Formula VI withdiphenyl carbonate or phenyl chloroformate in the presence of a basesuch as sodium hydride or pyridine.

Also, many compounds of Formula I can be prepared by reacting anappropriate sulfonyl isocyanate, V, with the appropriately substitutedaminoheterocycle, VI, as shown in Equation 3 below. ##STR12## wherein R,R₁, A and n are as previously defined; and

Q is Q-1 to Q-5, Q-10 to Q-17, Q-23 to Q-28, and Q-31 to Q-34.

The reaction is best performed in an inert solvent such as methylenechloride, tetrahydrofuran, acetonitrile or toluene at 23° to 100° C. for1 to 24 hours. In cases where the products are insoluble in the reactionsolvent, they may be isolated by simple filtration. When the productsare soluble, they may be isolated by evaporation of the solvent andtrituration of the residue with an appropriate solvent such as1-chlorobutane, diethyl ether, methanol or ethyl acetate and filtration.The products may be further purified by column chromatographyprocedures.

Sulfonyl isocyanates of Formula V above may be prepared, although oftentimes in low yields, from corresponding sulfonamides of Formula II bymethods analogous to those described in U.S. Pat. No. 4,238,621 and EP-ANo. 83,975 (published July 20, 1983). By a preferred method,sulfonamides are reacted with phosgene, in the presence of n-butylisocyanate and a tertiary amine catalyst, at reflux in an inert solventsuch as xylenes. A preferred catalyst is 1,4-diazabicyclo[2.2.2]octane(DABCO). Alternatively, isocyanates, V, may be prepared by (1) reactingsulfonamides, II, with n-butyl isocyanate and a base such as potassiumcarbonate at reflux in an inert solvent such as 2-butanone to form an-butyl sulfonylurea; and (2) reacting this compound with phosgene andDABCO catalyst at reflux in xylenes solvent.

Many sulfonamides of Formula II can be prepared by the sequence ofreactions shown below in Equation 4. ##STR13## wherein R₁ and n are aspreviously defined; and

Q is Q-1 to Q-34 and Q-45 to Q-54.

The reactions of Equation 4(a,b) can be run by methods analogous tothose described in EP-A Nos. 83,975 (published July 20, 1983) and 85,476(published Aug. 10, 1983). In Reaction 4(a) the methods require reactingamines of Formula VII with sodium nitrite in concentrated hydrochloricacid and acetic acid to form diazonium salts. Following addition andreaction of the diazonium salt suspensions with suspensions containingexcess sulfur dioxide and copper (I) chloride or copper (II) chloridecatalyst in acetic acid solvent, the sulfonyl chlorides, VIII, areisolated by addition of water, filtration if VIII is a solid, orextraction with methylene chloride if VIII is an oil. Generally, thesulfonyl chlorides, VIII, are pure enough to carry on to the next stepwithout further purification.

In Reaction 4(b), sulfonamides, IIa, are prepared by reacting sulfonylchlorides, VIII, with excess ammonia or aqueous ammonium hydroxide in aninert solvent such as tetrahydrofuran. Sulfonamides, IIa, are isolatedby filtration and washing with water to remove the by-product ammoniumchloride, and concentrating the organic solution. The sulfonamides maybe further purified by recrystallization or chromatography procedures.

Many sulfonyl chlorides of Formula VIII may also be prepared viaoxidative chlorination of the appropriate thioethers of Formula A, asillustrated in Equation 4a. ##STR14## wherein R₁ and Q do not contain athioether or alkenyl group;

R₁ ' is C₂ -C₃ alkyl or benzyl; and

Q is Q-1 to Q-34.

The reaction of Equation 4a may be carried out by contacting asuspension of the thioether A in a solvent such as acetic acid orpropionic acid in the presence of at least 2.5 equivalents of water withat least 3.0 equivalents of chlorine at about -10° to 30° C. for 0.25 to5 hours. The reaction is poured into ice-water and the product isisolated by filtration or extraction with a solvent such as methylenechloride. The extract is optionally washed with aqueous sodiumbicarbonate until neutral or slightly basic, then dried, and the solventis evaporated to yield a product generally pure enough to be carrieddirectly to the next step. Thioethers, A, may be prepared by analogywith methods described hereinafter in Equation 11a, or simplemodifications thereof, from appropriate corresponding thioetherscontaining ortho-functional groups, J, by those skilled in the art.

Certain sulfonamides of Formula II are preferably prepared fromappropriately substituted o-(methoxycarbonyl)alkanebenzenesulfonamidesof Formula IX, as shown below in Equation 5. ##STR15## wherein R₁ is aspreviously defined;

R₈ ^(') is CH₃, C₂ H₅, CF₂ H, CH₂ CH═CH₂ or CH₂ CN; and

M is Cl, Br or I; and n is 1.

Reaction 5(a)

The conversion of carboxylic esters to hydrazides is well known in theliterature. In a typical procedure, a carboxylic ester of Formula IX isreacted with an excess of hydrazine monohydrate (preferably 10 to 30%mole excess) in an inert solvent such as methanol or ethanol at refluxfor one to 24 hours. The hydrazides, X, are isolated by filtration or byconcentration to remove the solvent and triturating the hydrazideresidue, X, with water. The compounds are generally sufficiently pure tobe carried on directly to step 5(b), but may be purified further byrecrystallization procedures.

Reaction 5(b)

The conversion of hydrazides to 2-mercaptooxadiazoles is also well knownin the literature, e.g., R. W. Young and K. H. Wood, J. Am. Chem. Soc.,77, 400 (1955). In a typical procedure, hydrazides, X, are heated atreflux with equimolar amounts of potassium hydroxide and an excess ofcarbon disulfide in methanol or ethanol solvent until the evolution ofhydrogen sulfide has nearly stopped. By these conditions, however,thiadiazole XI is obtained from hydrazide X, based on mass spectrumanalysis. Thiadiazoles, XI, are isolated by concentration of thesolvent, addition of water to the residue, filtration of the aqueoussuspension to remove insoluble impurities, acidification of the aqueousfiltrate with hydrochloric acid and filtration. Compounds, XI, aregenerally pure enough to carry on to step 5(c), but may be furtherpurified by recrystallization procedures.

Reaction 5(c)

Thiadiazoles, XI, are alkylated by reaction with an equimolar amount ofbase such as potassium hydroxide and excess alkylating agent, XII, atreflux in an inert solvent such as methanol or ethanol for 0.5 to 24hours. Sulfonamides, IIb, are isolated by concentration of the solvent,addition of water to the residue and filtration. For the case where R₈^(') ═CF₂ H, the reaction is preferably run in N,N-dimethylformamide(DMF) solvent at 60°-90° C. with excess potassium carbonate as base.Following addition of water, sulfonamides, IIb, are isolated byfiltration; they may be purified by recrystallization procedures. Estersof the general Formula IX, where n is 1, are known; see U.S. Pat. No.4,348,219 (issued Sept. 7, 1982).

Sulfonamides of Formula II containing an o-methanepyridinyl,-pyrimidinyl, -pyrazinyl, -pyridazinyl or -triazinyl group (Q is Q-45 toQ-54) may be prepared by the sequence of reactions shown below inEquation 6. ##STR16## wherein R₁ is as originally defined, except R₁ maynot be Br; and

Q is Q-45 to Q-54.

The compounds of Formula IIc are prepared by analogy with the teachingsof EP-A No. 85,476 (published Aug. 10, 1983).

Reactions 6(a,b)

An N-t-butyl sulfonamide of Formula XIII is dissolved in an etherealsolvent, such as tetrahydrofuran, and two equivalents of n-butyllithiumin hexane are added at about -70° C. After 1-5 hours at about -70° C.,the compound of Formula XIV is formed. This is not isolated, but oneequivalent of a copper(I) iodide salt is added at about -70°, followedby 1-1.5 equivalents of an appropriately substituted heteroaromaticiodide of Formula XV. The reaction mixture is heated at 0° to 70° C. for1-3 days, concentrated and poured onto aqueous ammonia. Compounds ofFormula XVI are isolated by filtration if solids or by extraction withmethylene chloride and concentration if oils. The compounds, XVI, may befurther purified by recrystallization or chromatography procedures.

The compounds of Formula XV above may be prepared according to methodsknown in the art, such as those reviewed in "The Chemistry ofHeterocyclic Compounds", a series published by Interscience Publ., NewYork and London, the teachings of which are incorporated herein byreference. The iodopyridines are described in Vol. 14 of the aboveseries, pp. 407-488. Iodopyrimidines are described by D. J. Brown and S.F. Mason in Vol. 16 of the above series. The preparation ofiodopyrazines is taught by A. Hirshberg and P. E. Spoerri, J. Orq.Chem., 26, 1907 (1981) and iodopyridazines are described by D. L. Aldonsand R. N. Castle in Vol. 28 of the Interscience series, pp. 240-241. Theiodo-1,3,5-triazines are described by E. M. Smolin and L. Rapoport, inVol. 13 of the above series, and a method for preparingiodo-1,2,4-triazines is taught by A. Rykowski and H. C. van der Plas, inJ. Orq. Chem., 45, 881 (1980).

Reaction 6(c)

This reaction is conducted by heating a compound of Formula XVI with2-10 equivalents of trifluoroacetic acid or aqueous HBr with or withoutan inert solvent at 30°-70° for 1-3 days. The product, IIc, may beisolated as a trifluoroacetate or hydrobromide salt by evaporation ofsolvent and excess acid and trituration with ether. The free base may beobtained by neutralization of the salt with aqueous base, extractioninto an organic solvent, and concentration of the organic extracts.Products, IIc, may be further purified by recrystallization orchromatography procedures.

As shown in Equation 7 below, sulfonamides of Formula IIe containing atetrahydrofuran or tetrahydrothiophen group (Q is Q-35 to Q-38) may beprepared by catalytic reduction of the corresponding furan or thiophenegroups of sulfonamides of Formula IId (Q' is Q-31 to Q-34). ##STR17##wherein R₁ and n are as originally defined;

Q' is Q-31 to Q-34; and

Q is Q-35 to Q-38.

Selective reductions of the type shown in Equation 7 are well known inthe literature. The choice of catalyst, solvent, pressure andtemperature for reduction of furans has been reviewed by Samuel Sevadeshin "The Furans" by A. P. Dunlop and F. N. Peters, Reinhold PublishingCorporation, New York, N.Y. 1953, pp. 674-713; and by P. N. Rylander in"Catalytic Hydrogenation in Organic Synthesis", Academic Press, 1979,pp. 227-234. The reduction of thiophenes is reviewed by H. D. Hartoughin "Thiophene and Its Derivatives", The Chemistry of HeterocyclicCompounds Series, Interscience Publishers, Inc., New York, N.Y. 1952,pp. 167-169. Sulfonamides of Formula IId above are prepared fromappropriate anilines by the sequence of reactions described above inEquation 4.

Equation 8 below illustrates a method for preparing sulfonamides ofFormula IIf containing acetal or thioacetal groups (Q is Q-39 to Q-44).##STR18## wherein R₁ is as originally defined except R₁ is other than Bror CH₃ ;

n is as originally defined; and

Q is Q-39 to Q-44.

Reaction 8(a)

The compounds of Formula IIf are prepared by analogy with the teachingsof J. G. Lombardino, J. Orq. Chem., 36, 1843 and EP-A No. 85,476.

An appropriate N-t-butyl sulfonamide dissolved in tetrahydrofuransolvent is reacted with two equivalents of n-butyllithium in hexane at0° to 25° C. for 1-5 hours to form dilithio salts XVII. One equivalentof copper(I) iodide is then added at -20° to 0° C., followed by 1-1.5equivalents of an appropriate iodoalkylacetal or thioacetal of FormulaXVIII. The reaction mixture is heated at 0° to 70° C. for 1-3 days, thenworked up analogous to that described for Reaction 6(b) above to givecompounds of Formula XIX.

Reaction 8(b)

In this step the tert-butyl group is removed from XIX by heating thesecompounds in toluene in the presence of a catalytic amount ofp-toluenesulfonic acid (p-TSA). The products, IIf, are isolated andpurified by stripping the solvent, followed by recrystallization orchromatography procedures on the crude residues.

The anilines of Formula VII in Equation 4 above can be prepared byreduction of corresponding nitrobenzenes of Formula XX, as illustratedin Equation 9 below ##STR19## wherein R₁ is as originally defined; and

Q is Q-1 to Q-34 and Q-45 to Q-54.

The reduction reactions of Equation 9 can be run by methods known in theliterature by those skilled in the art. For details see, for example,EP-A Nos. 83,975 and 85,476 and references cited therein.

The nitrobenzenes of Formula XX above, containing ano-alkaneheterocyclic group, are important intermediates for thepreparation of many of the compounds of this invention. They can beprepared by those skilled in the art by the applicatiion of appropriatemethods selected from the variety of known literature procedures forpreparing substituted aromatic heterocycles.

For example, nitrobenzenes of Formula XXa, containing an o-alkylfuran or-thiophene group (Q is Q-31 to Q-34), can be prepared by analogy withthe teachings in EP-A No. 85,476, and references cited therein, asillustrated in Equation 10 below. ##STR20## wherein R₁ and n are asoriginally defined; and

Q is Q-31 to Q-34.

Thus, a furyl- or thienylcopper compound of Formula XXII is reacted withan o-(iodoalkyl)nitrobenzene of Formula XXI in an inert solvent such aspyridine or quinoline at 0° to 60° C. for 1-3 days. The product, XXa, isisolated by addition of an acid such as acetic acid and water,extraction with methylene chloride, stripping of solvent andchromatographing the crude product. The copper compounds of Formula XXIIare prepared by reacting the corresponding lithium compounds withcuprous iodide or cuprous bromide in an inert solvent such as ethylether. The detailed procedures for analogous types of reactions aredescribed in the following references: M. Nilsson and C. Ullenius, Acta.Chem. Scand., 24, 2379-2388 (1970); C. Ullenius, Acta. Chem. Scand., 26,3383-3386 (1972).

Nitrobenzenes of Formula XX containing an o-ethanepyrazinyl group (Q isQ-51) can be prepared by analogy with the teachings of J. Behun and R.Levine, J. Orq. Chem., 26, 3379 (1961). The method requires heatingmethylpyrazine with potassium hydroxide in the presence of excessamounts of an o-nitrobenzyl alcohol.

Nitrobenzenes of Formula XX, containing an o-ethanepyridyl group (Q isQ-45 to Q-47), can be prepared by reacting o-nitrobenzyl chlorides orbromides with methylpyridines in the presence of sodamide in liquidammonia. For details, refer to review publications for this type ofreaction, i.e., Bergstrom and Fernelius, Chem. Rev., 20, 413 (1937);Bergstrom, ibid. 35, 77 (1944) and Levine and Fernelius, ibid, 54, 449(1954); also see for general description of this type of reaction,"Pyridine and Its Derivatives", Vol. 14, Part, 2. pp. 169-170, of theseries "The Chemistry of Heterocyclic Compounds", A. Weissberger, Ed.

Nitrobenzenes of Formula XX containing an o-ethanepyrimidin-2-yl group(Q is Q-48) can be prepared by heating a1-(o-nitrophenyl)-2-amidinylethane hydrochloride salt with1,1,1,3-tetramethoxypropane in an inert solvent such as ethanol, amethod well known in the art for preparing 2-(alkyl)substitutedpyrimidines.

Many of the nitrobenzenes of Formula XX can be prepared by analogy withmethods described in EP-A No. 83,975 and references cited therein, asillustrated in Equation 11 below. ##STR21## wherein R₁ and n are asoriginally defined;

Q is Q-1 to Q-30; and

J are appropriate functional groups taught in EP-A 83,975, andreferences cited therein, to prepare o-groups Q-1 to Q-30.

The heterocyclic amines of Formula VI in Equation 3 above can beprepared by methods known in the literature, or simple modificationsthereof, by those skilled in the art. For instance, EP-A No. 84,224(published July 27, 1983) and W. Braker et al., J. Am. Chem. Soc., 69,3072 (1947) describe methods for preparing aminopyrimidines andtriazines substituted by acetal groups such as dialkoxymethyl or1,3-dioxolan-2-yl, among other groups. Also, for example, South Africanpatent application Nos. 825,045 and 825,671 describe methods forpreparing aminopyrimidines and triazines substituted by halogenoalkyl orhalogenalkylthio groups such as OCH₂ CH₂ F, OCH₂ CF₃, SCF₂ H or OCF₂ H,among other groups. Also, for example, South African patent applicationNo. 837,434 (published Oct. 5, 1983) describes methods for the synthesisof cyclopropylpyrimidines and triazines substituted by such groups asalkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino oralkoxyalkyl.

Also, the 5,6-dihydrofuro[2.3-d]pyrimidin-2-amines, thecyclopenta[d]pyrimidin-2-amines (VI, A is A-2) and the6,7-dihydro-5H-pyrano[2.3-d]pyrimidin-2-amines (VI, A is A-3) can beprepared as described in EP-A No. 15,683. Also, thefuro[2.3-d]pyrimidin-2-amines (VI, A is A-4) are described in EP-A No.46,677.

In addition, general methods for preparing aminopyrimidines andtriazines have been reviewed in the following publications:

"The Chemistry of Heterocyclic Compounds", a series published byInterscience Publishers, Inc., New York and London;

"Pyrimidines", Vol. 16 of the same series by D. J. Brown;

"s-Triazines and Derivatives", Vol. 13 of the same series by E. M.Smolin and L. Rappoport; and

F. C. Schaefer, U.S. Pat. No. 3,154,547 and K. R. Huffman and F. C.Schaefer, J. Orq. Chem., 28, 1812 (1963), which describe the synthesisof triazines.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydroxide). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by direct contactof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali or quaternary amine salt) with a solution containing the cationto be exchanged. This method is most effective when the desired saltcontaining the exchanged cation is insoluble in water and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged for that of the original salt and the desiredproduct is eluted from the column. This method is particularly usefulwhen the desired salt is water-soluble, e.g., a potassium, sodium orcalcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is furtherillustrated by the following specific examples. Unless otherwiseindicated, temperatures are in degrees centigrade.

EXAMPLE 1 2-(Aminosulfonyl)benzeneacetic acid, hydrazide

To a suspension of 30 g of methyl 2-(aminosulfonyl)benzeneacetate in 125ml of absolute ethanol was added 7.8 g of hydrazine monohydrate. Thesuspension was heated at reflux for about 16 hours, then cooled in anice-water bath. A viscous oil formed which solidified on continuedstirring and cooling. The suspension was filtered and suction-dried togive 23 g of the subject compound; m.p. 116°-125° C. Anal. Calc. for: C₈H₁₁ N₃ O₃ S; C,41.9; H,4.8; N,18.3. Found: C,41.5; H,4.9; N,18.0.

EXAMPLE 2 2-[(5-Mercapto-1,3,4-thiadiazol-2-yl)methyl]benzenesulfonamide

To a suspension of 22 g of the hydrazide prepared in Example 1 in 175 mlof absolute ethanol was added a solution of 5.4 g of potassium hydroxidein 40 ml of water. After stirring several minutes, 9.2 g of carbondisulfide was added dropwise. The suspension was refluxed 4 hours thenconcentrated in vacuo. After water (about 200 ml) was added to theresidue and the suspension stirred several minutes, the suspension wasfiltered, and the filtrate was acidified with concentrated hydrochloricacid (red to litmus paper). The mixture was filtered and the solidisolated was suction-dried to give 5 g of the crude subject compound;m.p. 173°-197° C.

EXAMPLE 32-[[5-(Methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

To a solution containing 1.0 g of potassium hydroxide in 50 ml ofmethanol was added 5 g of the crude oxadiazole prepared in Example 2.After stirring about five minutes, 3.5 g of methyl iodide was added. Thesolution was refluxed one hour, cooled to 30°, an extra 10 ml of methyliodide was added, and the solution was refluxed an additional two hours,then concentrated in vacuo. After water (about 150 ml) was added to theresidue, the suspension was extracted with methylene chloride. Themethylene chloride solution was dried (MgSO₄), concentrated in vacuo,and the residue was recrystallized from acetonitrile to give 0.8 g ofthe subject compound; m.p. 175°-178° C. NMR(CDCl₃, DMSO-d₆): δ 2.8(s,SCH₃); 4.9(s, CH₂); 7.3(s, NH₂); 7.4-8.3 (m, ar) ppm. Mass spectrum bydirect probe using electron impact ionization showed highest significantm/e 301.

EXAMPLE 4N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

To a suspension containing 0.63 g of the sulfonamide prepared in Example3 in 10 ml of p-dioxane was added 0.6 gphenyl(4,6-dimethoxypyrimidin-2-yl)carbamate followed by dropwiseaddition of 0.33 g of 1.8-diazabicyclo[5.4.0]undec-7-ene (DBU). Thesolution was stirred at room temperature for two hours then diluted withabout 75 ml of water. After extracting the cloudy aqueous solution 1×30ml of diethyl ether, the clear aqueous layer was acidified withconcentrated hydrochloric acid (red to litmus paper), and the suspensionwas filtered. The residue was triturated with 5 ml of warm ethyl acetateto give 0.2 g of the subject compound; m.p. 171°-175° C. NMR (CDCl₃,DMSO-d₆): δ 2.7(s, SCH₃); 4.0(s, OCH₃); 4.95(s, CH₂); 5.9(s, pyrimidineH); 7.6-8.4(m, ar); 9.8(s, NH) ppm.

EXAMPLE 5N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-[[5-(methylthio)-1,3,4-thiadiazol-2-yl]methyl]-benzenesulfonamide

By the procedure of Example 4, 0.3 g of the sulfonamide prepared inExample 3 was reacted with 0.29 g ofphenyl(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate and 0.15 g of"DBU" in 10 ml of p-dioxane. After stirring two hours at roomtemperature the solution was diluted with about 75 ml of water andacidified with concentrated hydrochloric acid (red to litmus paper).Following filtration, the residue was washed with water (2×20ml) thenwith ether (1×20ml) and suction-dried to give 0.15 g of the subjectcompound; m.p. 140°-146° C. NMR (CDCl₃): δ2.6(d,6H,SCH₃, OCH₃); 4.1 (S,3H, CH₃); 4.9(S, 2H, CH₂); 7.4-7.7(m, 4H, Ar+NH); 8.3(d, 1H, Ar).

EXAMPLE 6 1-[[2-(Phenylmethylthio)phenyl]methyl]-1H-1,2,4-triazole

To a suspension of 9.9 g of potassium t-butoxide in 100 ml of DMF undera N₂ atmosphere was added portion wise 6 g of 1,2,4-triazole. Afterstirring at ambient temperature for one hour, a solution of 20 g of2-benzylmercaptobenzyl chloride in 15 ml of DMF was added dropwise andthe suspension was heated at 70° C. for 4 hours, then stirred at 25° C.16 hours. After pouring the suspension into excess ice-water the residuewas extracted with methylene chloride, dried (MgSO₄), and the solventwas evaporated in vacuo to an oil residue which solidified to 14.5 g ofthe subject compound when triturated with 1-chlorobutane; m.p. 65°-68°C.

EXAMPLE 7 2-[(1H-1,2,4-triazol-1yl)methyl]benzenesulfonamide

(a) To a solution of 10 g of the product of Example 6 and 1.9 g of waterin 100 ml of propionic acid was added dropwise 9.1 ml of chlorine; thetemperature of the resulting reaction was maintained at -5° to 0° C.with external cooling. After stirring at 0° for one hour the suspensionwas cooled to -20° C. and filtered. The residue was washed with 40 ml ofhexane and suction-dried to yield 4 g of2-[(1H-1,2,4-triazol-1-yl)methyl]benzenesulfonyl chloride as a crudesolid; m.p. 180°-195° C.

(b) To a suspension of 3 g of the above sulfonyl chloride in 125 ml oftetrahydrofuran was added dropwise about 25 ml of concentrated aqueousNH₄ OH at 10° to 19° C. with external cooling. After stirring at 25° C.one hour, the organic solvent (tetrahydrofuran) was evaporated in vacuoand the residue was diluted with excess ice-water, then filtered. Theisolated solid was dried in 100 ml of tetrahydrofuran over MgSO₄ and,after evaporation of the solvent, the oil residue was triturated with1-chlorobutane to yield 1.7 g of the subject compound; m.p. 128°-131° C.NMR(CDCl₃):ppm 5.9(d, 4H, CH₂ +SO₂ NH₂) 7.3-7.6(m, 4H, Ar)7.9 and8.3(2S, 2H, tri 2H) 8.1(m, 1H, Ar).

EXAMPLE 8N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-[(1H-1,2,4-triazol-2-yl)methyl]benzenesulfonamide

By the procedure of Example 4, 0.4 g of the product of Example 7 wasreacted with 0.52 g of phenyl(4,6-dimethoxypyrimidin-2-yl)carbamate and0.26 g of "DBU" in 10 ml of p-dioxane. After stirring at 25° C. for twohours, the resulting suspension was diluted with about 50 ml of water,and filtered; the resulting filtrate was acidified with concentratedhydrochloric acid to pH 4, then filtered. The residue was washed 2×10 mlwater, suction-dried 16 hours, then triturated with about 10 ml of warmethyl acetate to yield 0.5 g of the subject compound; m.p. 219°-220° C.IR(nujol): 1690 cm⁻¹ (c=o); NMR(CDCl₃): ppm 3.9(S, 6H, OCH₃); 5.8(S, 1H,py H); 6.0(S, 2H, CH₂); 7.9 and 8.2(2S, 2H, tri 2H); 7.1-7.6(m, 4H,Ar+NH); 8.15(m, 1H, Ar).

Using the techniques described in Equations 1-11 and Examples 4, 5 and8, or simple modifications thereof, obvious to one skilled in the art,the following compounds in Tables I-V can be made.

                                      TABLE I                                     __________________________________________________________________________     ##STR22##                                                                    Q                R  R.sub.1                                                                            n X      Y        m.p. °C.                    __________________________________________________________________________    Q-1 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-1 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-1 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-1 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    1 Cl     OCH.sub.3                                   Q-1 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-1 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          CH.sub.3                                                                         H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-1 (R.sub.5 = CH.sub.3, R.sub.6 = CH.sub.3)                                                   H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-1 (R.sub.5 = CH.sub.3, R.sub.6 = CH.sub.3)                                                   H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-2 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-2 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-2 (R.sub.5 = H, R.sub.6 = CH.sub.3                                                           H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-2 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    1 Cl     OCH.sub.3                                   Q-2 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-2 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    2 OCH.sub.3                                                                            CH.sub.3                                    Q-2 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          CH.sub.3                                                                         H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-2 (R.sub.5 = CH.sub.3, R.sub.6 = CH.sub.3)                                                   H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-2 (R.sub.5 = CH.sub.3, R.sub.6 = CH.sub.3)                                                   H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-3 (R.sub.5 = CH.sub.3)                                                                       H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-3 (R.sub.5 = CH.sub.3)                                                                       H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-3 (R.sub.5 = CH.sub.3)                                                                       H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-3 (R.sub.5 = CH.sub.3)                                                                       H  H    1 Cl     OCH.sub.3                                   Q-3 (R.sub.5 = CH.sub.3)                                                                       H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-3 (R.sub.5 = CH.sub.3)                                                                       CH.sub.3                                                                         H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-4 (R.sub.5 = H, R.sub.6 =  CH.sub.3)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-4 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-5 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-5 (R.sub.5 =  CH.sub.3, R.sub.6 =  H)                                                        H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-6 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-7 (R.sub.5 = H, R.sub.6 = H)                                                                 H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-6 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-7 (R.sub.5 = H, R.sub.6 = H)                                                                 H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-8 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-8 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                          H  H    2 OCH.sub.3                                                                            CH.sub.3                                    Q-9 (R.sub.5, R.sub.6, R.sub.7 = H)                                                            H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-9 (R.sub.5, R.sub.6, R.sub.7 = H)                                                            H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-9 (R.sub.5, R.sub.6, R.sub.7 = H)                                                            H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-9 (R.sub.5, R.sub.6, R.sub.7 = H)                                                            H  H    1 Cl     OCH.sub.3                                   Q-9 (R.sub.5, R.sub.6, R.sub.7 = H)                                                            H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-9 (R.sub.5, R.sub.7 = CH.sub.3 ; R.sub.6 = H)                                                H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             CH.sub.3 205-206                            Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                            OCH.sub.3                                                                              171-174                            Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             OCH.sub.3                                                                              170-172                            Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 Cl     OCH.sub.3                                                                              167-171                            Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    2 CH.sub.3                                                                             CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    2 CH.sub.3                                                                             OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    2 Cl     OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     CH.sub.3                                                                         H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SC.sub.2 H.sub.5)                                                              H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-13 (R.sub.8 = SC.sub.2 H.sub.5)                                                              H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SC.sub.2 H.sub.5)                                                              H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-13 (R.sub.8 = SC.sub.2 H.sub.5)                                                              H  H    1 Cl     OCH.sub.3                                   Q-13 (R.sub.8 = SC.sub.2 H.sub.5)                                                              H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub. 3                                                                           OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 Cl     OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = SC.sub.2 H.sub.5)                                                              H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 Cl     OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = OC.sub.2 H.sub.5)                                                              H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 Cl     OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-13 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-13 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 Cl     OCH.sub.3                                   Q-13 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-14 (R.sub.9 = Cl)                                                                            H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-14 (R.sub.9 = Cl)                                                                            H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-14 (R.sub.9 = Cl)                                                                            H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-14 (R.sub.9 = Cl)                                                                            CH.sub.3                                                                         H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-17             H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-17             H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-17             H  H    1 Cl     OCH.sub.3                                   Q-18 (R.sub.5 = CH.sub.3)                                                                      H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-19 (R.sub.5 = CH.sub.3)                                                                      H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-20 (R.sub.5 = H, R.sub.6 = H)                                                                H  H    1 OCH.sub.3                                                                            OCH.sub.3                                                                              219-220                            Q-20 (R.sub.5 = H, R.sub.6 = H)                                                                H  H    1 CH.sub.3                                                                             OCH.sub.3                                                                              215-218                            Q-20 (R.sub.5 = H, R.sub.6 = H)                                                                H  H    1 CH.sub.3                                                                             CH.sub.3 206-208                            Q-20 (R.sub.5 = H, R.sub.6 = H)                                                                H  H    1 Cl     OCH.sub.3                                                                              224-226                            Q-20 (R.sub.5 = H, R.sub.6 = H)                                                                H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-20 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-20 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-21 (R.sub.5 = CH.sub.3)                                                                      H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-22 (R.sub.5 = H, R.sub.6 = H)                                                                H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-23 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-23 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                         H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-23 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-23 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                         H  H    1 Cl     OCH.sub.3                                   Q-23 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-24 (R.sub.5 = CH.sub.3 l, R.sub.6 = H)                                                       H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-24 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-24 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                         H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-24 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 Cl     OCH.sub.3                                   Q-25 (R.sub.5 = CH.sub.3, R.sub.6 = H)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-26 (R.sub.5 = CH.sub.3, R.sub.6 = CH.sub.3)                                                  H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-27 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-28 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-29 (R.sub.5 = H, R.sub.6 = CH.sub.3)                                                         H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-30 (R.sub.5 R.sub.7 = H)                                                                     H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-30 (R.sub.5, R.sub.6 = H; R.sub.7 = CH.sub.3)                                                H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-31 (R.sub.5 R.sub.7 = CH.sub.3)                                                              H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-31 (R.sub.5 R.sub.7 =  CH.sub.3)                                                             H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-31 (R.sub.5, R.sub.6 = H; R.sub.7 = CH.sub.3)                                                H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-32 (R.sub.5 R.sub.7 = H)                                                                     H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-33 (R.sub.5 R.sub.7 = CH.sub.3)                                                              H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-34 (R.sub.5 R.sub.7 = H                                                                      H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-35 (R.sub.5 R.sub.7 = H                                                                      H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-35 (R.sub.5, R.sub.6 = H; R.sub.7 = CH.sub.3)                                                H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-36 (R.sub.5 R.sub.7 = H)                                                                     H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-37 (R.sub.5 R.sub.7 = H)                                                                     H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-37 (R.sub.5 R.sub.7 = H)                                                                     H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-38 (R.sub.5 R.sub.7 = H)                                                                     H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-40 (R.sub. 5 = HH)                                                                              H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-41 (R.sub.5 = H)                                                                             H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-43 (R.sub.5 = H)                                                                             H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-44 (R.sub.5 = H)                                                                             H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-45 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-46 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-47 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-48 (R.sub.5, R.sub.11, R.sub.12 = CH.sub.3)                                                  H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-48 (R.sub.11, R.sub.12 = OCH.sub.3 ; R.sub.5 = H)                                            H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-48 (R.sub.5 = H; R.sub.11, R.sub.12 = CH.sub.3)                                              H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-48 (R.sub.5, R.sub.11, R.sub.12 = CH.sub.3)                                                  H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-49 (R.sub.11, R.sub.12 = CH.sub.3)                                                           H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-50 (R.sub.11, R.sub.12 = CH.sub.3)                                                           H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-51 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-52 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-53 (R.sub.13, R.sub.14 = CH.sub.3)                                                           H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-53 (R.sub.13, R.sub.14 = OCH.sub.3)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-54 (R.sub.13, R.sub.14 = CH.sub.3)                                                           H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-54 (R.sub.13, R.sub.14 = OCH.sub.3)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  6-Cl 1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  6-CH.sub.3                                                                         1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 I(R.sub.8 = SCH.sub.3)                                                                    H  5-CF.sub.3                                                                         1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  5-OCH.sub.3                                                                        1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.3)                                                                     H  5-OCF.sub.2 H                                                                      1 OCH.sub.3                                                                            OCH.sub.3                                   Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  6-SCF.sub.2 H                                                                      2 OCH.sub.3                                                                            OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OC.sub.2 H.sub.5                                                                     CH.sub.3                                    Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 F      OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.2 CH.sub.3)                                                            H  H    1 Br     OCH.sub.3                                   Q-24 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 CH.sub.2 F                                                                           CH.sub.3                                    Q-14 (R.sub.9 = Cl)                                                                            H  H    1 OCH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                    Q-1 (R.sub.5, R.sub.6 = CH.sub.3)                                                              H  H    1 OCH.sub.2 CHF.sub.2                                                                  CH.sub.3                                    Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  H    1 OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 F      OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 I      OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.2 CH.sub.3)                                                            H  H    1 OCF.sub.2 H                                                                          OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.2 CH.sub.3)                                                            H  H    1 CH.sub.2 F                                                                           CH.sub.3                                    Q-10 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 OCH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.2 CHF.sub.2                                                                  CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CF.sub.3                                                                             OCH.sub.3                                   Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                            H                                           Q-1 (R.sub.5, R.sub.6 = CH.sub.3)                                                              H  H    2 Cl     OC.sub.2 H.sub.5                            Q-2 (R.sub.5, R.sub.6 = CH.sub.3)                                                              H  H    1 OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                          Q-3 (R.sub. 5 = CH.sub.3)                                                                      H  H    1 Cl     NHCH.sub.3                                  Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 OC.sub.2 H.sub.5                                                                     N(OCH.sub.3)CH.sub.3                        Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             N(CH.sub.3).sub.2                           Q-6 (R.sub.5, R.sub.6 = CH.sub.3)                                                              H  H    1 OCH.sub.3                                                                            C.sub.2 H.sub.5                             Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    2 OCH.sub.3                                                                            OCH.sub.2 CH = CH.sub.2                     Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             OCH.sub.2 CCH                               Q-14 (R.sub.9 = Cl)                                                                            H  H    1 CH.sub.3                                                                             OCH.sub.2 CH.sub.2 OCH.sub.3                Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             CH.sub.2 SCH.sub.3                          Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             CHO                                         Q-24 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 CH.sub.3                                                                              ##STR23##                                  Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                            CH(OCH.sub.3).sub.2                         Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  H    2 OCH.sub.3                                                                            CH(OC.sub.2 H.sub.5).sub.2                  Q-31 (R.sub.5, R.sub.6, R.sub.7 = CH.sub.3)                                                    H  H    1 OCH.sub.3                                                                            CH(SCH.sub.3).sub.2                         Q-35 (R.sub.5, R.sub.6, R.sub.7 = H)                                                           H  H    1 OCH.sub.3                                                                            C(CH.sub.3)(OCH.sub.3).sub.2                Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                             ##STR24##                                  Q-1 (R.sub.5, R.sub.6 = CH.sub.3)                                                              H  H    1 OCH.sub.3                                                                             ##STR25##                                  Q-2 (R.sub.5, R.sub.6 = CH.sub.3)                                                              H  H    1 OCH.sub.3                                                                             ##STR26##                                  Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                             ##STR27##                                  Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  H    2 OCH.sub.3                                                                             ##STR28##                                  Q-3 (R.sub.5 = CH.sub.3)                                                                       H  H    1 OCH.sub.3                                                                             ##STR29##                                  Q-24 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    1 OCH.sub.3                                                                             ##STR30##                                  Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 CH.sub.3                                                                             SCF.sub.2 H                                 Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 Cl     OCF.sub.2 H                                 Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                             ##STR31##                                  Q-51 (R.sub.5, R.sub.6 = CH.sub.3 )                                                            H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-48 (R.sub.5, R.sub.11, R.sub.12 = CH.sub.3)                                                  H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-45 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-46 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-47 (R.sub.5, R.sub.6 = CH.sub.3)                                                             H  H    2 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.2 CHCH.sub.2)                                                          H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-13 (R.sub.8 = SCH.sub.2 CHCH.sub.2)                                                          H  H    1 OCH.sub.3                                                                            CH.sub.3                                    Q-13 (R.sub.8 = SCH.sub.2 CHCH.sub.2)                                                          H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.2 CHCH.sub.2)                                                          H  H    1 Cl     OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-13 (R.sub.8 =  SCH.sub.2 CN)                                                                 H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13 (R.sub.8 = SCH.sub.2 CN)                                                                  H  H    1 Cl     OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                          Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 OCF.sub.2 H                                                                          CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.3)                                                                     H  H    1 Br     OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.3)                                                                     H  H    1 OC.sub.2 H.sub.5                                                                     CH.sub.3                                    Q-10 (R.sub.8 = SCH.sub.2 CH.sub.3)                                                            H  H    1 OCF.sub.2 H                                                                          OCH.sub.3                                   Q-10 (R.sub.8 = OCH.sub.2 CH.sub.3)                                                            H  H    1 OCF.sub.2 H                                                                          CH.sub.3                                    Q-10 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 OCH.sub.3                                                                            CH(OCH.sub.3).sub.2                         Q-10 (R.sub.8 = SCF.sub.2 H)                                                                   H  H    1 OCH.sub.3                                                                            CH.sub.2 OCH.sub.3                          Q-9 (R.sub.5, R.sub.7 = CH.sub.3, R.sub.6 = H)                                                 H  H    1 OCH.sub.3                                                                            OCH.sub.3                                   Q-9 (R.sub.5, R.sub.7 =  CH.sub.3, R.sub.6 = H)                                                H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-9 (R.sub.5, R.sub.7 = CH.sub.3, R.sub.6 = H)                                                 H  H    1 Cl     OCH.sub.3                                   Q-9 (R.sub.5, R.sub.7 = CH.sub.3, R.sub.6 = H)                                                 H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-13 (R.sub.8 = SH)                                                                            H  H    1 CH.sub.3                                                                             OCH.sub.3                                   Q-13 (R.sub.8 = SH)                                                                            H  H    1 CH.sub.3                                                                             CH.sub.3                                    Q-13 (R.sub.8 = SH)                                                                            H  H    1 Cl     OCH.sub.3                                   Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  H    2 CH.sub.3                                                                             OCH.sub.3                                   Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  H    2 CH.sub.3                                                                             CH.sub.3                                    Q-20 (R.sub.5, R.sub.6 = H)                                                                    H  H    2 Cl     OCH.sub.3                                   __________________________________________________________________________

                                      TABLE II                                    __________________________________________________________________________     ##STR32##                                                                    Q                R.sub.1                                                                            R  n X      Y        m.p. °C.                    __________________________________________________________________________    Q-1                                                                              (R.sub.5,R.sub.6 = Ch.sub.3)                                                                H    H  1 OCH.sub.3                                                                            Ch.sub.3                                    Q-1                                                                              (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-1                                                                              (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-1                                                                              (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    CH.sub.3                                                                         1 OCH.sub.3                                                                            CH.sub.3                                    Q-1                                                                              (R.sub.5 = CH.sub.3,R.sub.6 = H)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-1                                                                              (R.sub.5 = H,R.sub.6 =  CH.sub.3)                                                           H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-2                                                                              (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-2                                                                              (R.sub.5 = CH.sub.3,R.sub.6 = H)                                                            H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-2                                                                              (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-2                                                                              (R.sub.5 = CH.sub.3,R.sub.6 = H)                                                            H    CH.sub.3                                                                         1 CH.sub.3                                                                             OCH.sub.3                                   Q-2                                                                              (R.sub.5 = CH.sub.3,R.sub.6 = CH.sub.3)                                                     H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-2                                                                              (R.sub.5 = CH.sub.3,R.sub.6 = CH.sub.3)                                                     H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-3                                                                              (R.sub.5 = CH.sub.3)                                                                        H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-3                                                                              (R.sub.5 = CH.sub.3)                                                                        H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-4                                                                              (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-4                                                                              (R.sub.5 =  CH.sub.3,R.sub.6 = H)                                                           H    H  2 OCH.sub.3                                                                            OCH.sub.3                                   Q-5                                                                              (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-6                                                                              (R.sub.5 = CH.sub.3,R.sub.6 = H)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-7                                                                              (R.sub.5 = H,R.sub.6 = H)                                                                   H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-8                                                                              (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-9                                                                              (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-9                                                                              (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-9                                                                              (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-9                                                                              (R.sub.5,R.sub.7 = CH.sub.3 ; R.sub.6 = H)                                                  H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  1 OCH.sub.3                                                                            CH.sub.3 140-146                            Q-13                                                                             (R.sub.8 =  SCH.sub.3)                                                                      H    H  1 OCH.sub.3                                                                            OCH.sub.3                                                                              155-159                            Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    CH.sub.3                                                                         1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SC.sub.2 H.sub.5)                                                                H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SC.sub.2 H.sub.5)                                                                H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10                                                                             (R.sub.8 = SC.sub.2 H.sub.5)                                                                H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    CH.sub.3                                                                         1 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = C.sub.2 H.sub.5)                                                                 H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = OC.sub.2 H.sub.5)                                                                H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-10                                                                             (R.sub.8 = OC.sub.2 H.sub.5)                                                                H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10                                                                             (R.sub.8 = OC.sub.2 H.sub.5)                                                                H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = OC.sub.2 H.sub.5)                                                                H    CH.sub.3                                                                         1 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = SH)                                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = SH)                                                                              H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13                                                                             (R.sub.8 = SCF.sub.2 H)                                                                     H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCF.sub.2 H)                                                                     H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13                                                                             (R.sub.8 = SCF.sub.2 H)                                                                     H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCF.sub.2 H)                                                                     H    CH.sub.3                                                                         1 CH.sub.3                                                                             OCH.sub.3                                   Q-14                                                                             (R.sub.9 = Cl)                                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-14                                                                             (R.sub.9 = Cl)                                                                              H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-14                                                                             (R.sub.9 = Cl)                                                                              H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-14                                                                             (R.sub.9 = Cl)                                                                              H    CH.sub.3                                                                         1 OCH.sub.3                                                                            CH.sub.3                                    Q-17             H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-17             H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-18                                                                             (R.sub.5 = CH.sub.3)                                                                        H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-19                                                                             (R.sub.5 = CH.sub.3)                                                                        H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-20                                                                             (R.sub.5,R.sub.6 = H)                                                                       H    H  1 OCH.sub.3                                                                            CH.sub.3 179-182                            Q-20                                                                             (R.sub.5,R.sub.6 = H)                                                                       H    H  1 OCH.sub.3                                                                            OCH.sub.3                                                                              183-186                            Q-20                                                                             (R.sub.5,R.sub.6 = H)                                                                       H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-20                                                                             (R.sub.5 = CH.sub.3,R.sub.6 = H)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-20                                                                             (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-21                                                                             (R.sub.5 = CH.sub.3)                                                                        H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-22                                                                             (R.sub.5 = H,R.sub.6 = H)                                                                   H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-23                                                                             (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-24                                                                             (R.sub.5 = CH.sub.3,R.sub.6 = H)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-25                                                                             (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-26                                                                             (R.sub.5 = CH.sub.3,R.sub.6 = CH.sub.3)                                                     H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-27                                                                             (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-28                                                                             (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-29                                                                             (R.sub.5 = H,R.sub.6 = CH.sub.3)                                                            H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-30                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-30                                                                             (R.sub.5,R.sub.6 = H; R.sub.7 = CH.sub.3)                                                   H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-31                                                                             (R.sub.5,R.sub.6,R.sub.7 = CH.sub.3)                                                        H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-31                                                                             (R.sub.5,R.sub.6 ,R.sub.7 = CH.sub.3)                                                       H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-31                                                                             (R.sub.5,R.sub.6 = H; R.sub.7 = CH.sub.3)                                                   H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-32                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-33                                                                             (R.sub.5,R.sub.6,R.sub.7 = CH.sub.3)                                                        H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-34                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-35                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-35                                                                             (R.sub.5,R.sub.6 = H; R.sub.7 = CH.sub.3)                                                   H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-36                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-37                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-37                                                                             (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-38                                                                             (R.sub.5,R.sub.6,R.sub.7 =  H)                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-40                                                                             (R.sub.5 = H) H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-41                                                                             (R.sub.5 = H) H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-43                                                                             (R.sub.5 = H) H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-44                                                                             (R.sub.5 = H) H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-45                                                                             (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-46                                                                             (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-47                                                                             (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-48                                                                             (R.sub.5,R.sub.11,R.sub.12 = CH.sub.3)                                                      H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-48                                                                             (R.sub.5,R.sub.11,R.sub.12 = CH.sub.3)                                                      H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-48                                                                             (R.sub.11,R.sub.12 = OCH.sub.3 ; R.sub.5 = H)                                               H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-48                                                                             (R.sub.5 = H; R.sub.11,R.sub.12 = CH.sub.3)                                                 H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-48                                                                             (R.sub.5,R.sub.11,R.sub.12 = CH.sub.3)                                                      H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-49                                                                             (R.sub.11,R.sub.12 = CH.sub.3)                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-50                                                                             (R.sub.11,R.sub.12 = CH.sub.3)                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-51                                                                             (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-52                                                                             (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-53                                                                             (R.sub.13,R.sub.14 = CH.sub.3)                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-53                                                                             (R.sub.13,R.sub.14 = OCH.sub.3)                                                             H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-54                                                                             (R.sub.13,R.sub.14 = CH.sub.3)                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-54                                                                             (R.sub.13,R.sub.14 = OCH.sub.3)                                                             H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCH.sub.3)                                                                       6-Cl H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCH.sub.3)                                                                       6-CH.sub.3                                                                         H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCH.sub.3)                                                                       5-CF.sub.3                                                                         H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-13                                                                             (R.sub.8 = SCH.sub.3)                                                                       5-OCH.sub.3                                                                        H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-13                                                                             (R.sub.8 = SCH.sub.3)                                                                       5-OCF.sub.2 H                                                                      H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-20                                                                             (R.sub.5,R.sub.6 = H)                                                                       6-SCF.sub.2 H                                                                      H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  1 CH.sub.3                                                                             OC.sub.2 H.sub.5                            Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  1 OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                  Q-14                                                                             (R.sub.9 = Cl)                                                                              H    H  1 OCF.sub.2 H                                                                          N(OCH.sub.3)CH.sub.3                        Q-1                                                                              (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            N(CH.sub.3).sub.2                           Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  1 OCH.sub.3                                                                            C.sub.2 H.sub.5                             Q-2                                                                              (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  1 OCH.sub.3                                                                            SCH.sub.3                                   Q-3                                                                              (R.sub.5 = CH.sub.3)                                                                        H    H  1 OCH.sub.3                                                                            OCH.sub.2 CH CH.sub.2                       Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  1 CH.sub.3                                                                             CH(OCH.sub.3).sub.2                         Q-9                                                                              (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H    H  1 OCH.sub.2 CF.sub.3                                                                   CH.sub.3                                    Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  1 OCH.sub.2 CF.sub.3                                                                   OCH.sub.3                                   Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  1 OCH.sub.3                                                                            C(CH.sub.3)(OCH.sub.3).sub.2                Q-24                                                                             (R.sub.5,R.sub.6 =CH.sub.3)                                                                 H    H  1 OCH.sub.3                                                                             ##STR33##                                  Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  1 OCH.sub.3                                                                             ##STR34##                                  Q-51                                                                             (R.sub.5,R.sub.6 = CH.sub.3)                                                                H    H  2 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SCH.sub.2 CH = CH.sub.2)                                                         H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-13                                                                             (R.sub.8 = SCH.sub.2 CH = CH.sub.2)                                                         H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-13                                                                             (R.sub.8  = SCH.sub.2 CH = CN)                                                              H    H  1 CH.sub.3                                                                             OCH.sub.3                                   Q-13                                                                             (R.sub.8 = SCH.sub.2 CN)                                                                    H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   Q-10                                                                             (R.sub.8 = OCH.sub.3)                                                                       H    H  1 OCH.sub.2 CH.sub.2 F                                                                 CH.sub.3                                    Q-10                                                                             (R.sub.8 = SCH.sub.3)                                                                       H    H  1 OCH.sub.2 CH.sub.2 F                                                                 OCH.sub.3                                   Q-20                                                                             (R.sub.5,R.sub.6 = H)                                                                       H    H  1 OC.sub.2 H.sub.5                                                                     NHCH.sub.3                                  Q-13                                                                             (R.sub.8 = SH)                                                                              H    H  1 OCH.sub.3                                                                            CH.sub.3                                    Q-13                                                                             (R.sub.8 = SH)                                                                              H    H  1 OCH.sub.3                                                                            OCH.sub.3                                   __________________________________________________________________________

                  TABLE III                                                       ______________________________________                                         ##STR35##                                                                    Q             R     R.sub.1                                                                             N   X.sub.1                                                                              Y.sub.1                                                                            m.p. °C.                     ______________________________________                                        Q-1  (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             O                                      Q-2  (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             O                                      Q-3  (R.sub.5 = H)                                                                              H     H   1   CH.sub.3                                                                             O                                      Q-9  (R.sub.5,R.sub.6,R.sub.7 = H)                                                              H     H   1   CH.sub.3                                                                             O                                      Q-9  (R.sub.5,R.sub.6,R.sub.7 = H)                                                              H     H   2   CH.sub.3                                                                             O                                      Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   CH.sub.3                                                                             O                                      Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   OCH.sub.3                                                                            O                                      Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   OC.sub.2 H.sub.5                                                                     O                                      Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   OCF.sub.2 H                                                                          O                                      Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.2                               Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   OCH.sub.3                                                                            CH.sub.2                               Q-10 (R.sub.8 = SCH.sub.3)                                                                      H     H   2   CH.sub.3                                                                             O                                      Q-10 (R.sub.8 = CH.sub.3)                                                                       H     H   1   CH.sub.3                                                                             O                                      Q-10 (R.sub.8 = CH.sub.3)                                                                       H     H   1   OCH.sub.3                                                                            O                                      Q-11 (R.sub.5 = H)                                                                              H     H   1   CH.sub.3                                                                             O                                      Q-12 (R.sub.5 = CH.sub.3)                                                                       H     H   1   OCH.sub.3                                                                            O                                      Q-14 (R.sub.9 = Cl)                                                                             H     H   1   CH.sub.3                                                                             O                                      Q-20 (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             O                                      Q-20 (R.sub.5,R.sub.6 = H)                                                                      H     H   2   CH.sub.3                                                                             O                                      Q-24 (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             O                                      Q-48 (R.sub.5,R.sub. 11,R.sub.12 = H)                                                           H     H   1   CH.sub.3                                                                             O                                      Q-10 (R.sub.8 =0 H)                                                                             H     H   1   CH.sub.3                                                                             O                                      ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                         ##STR36##                                                                    Q              R     R.sub.1                                                                              n   X.sub.1 m.p. °C.                       ______________________________________                                        Q-1  (R.sub.5,R.sub.6 = H)                                                                       H     H    1   CH.sub.3                                    Q-2  (R.sub.5,R.sub.6 = H)                                                                       H     H    1   OCH.sub.3                                   Q-3  (R.sub.5 = H) H     H    1   CH.sub.3                                    Q-9  (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H     H    1   CH.sub.3                                    Q-9  (R.sub.5,R.sub.6,R.sub.7 = H)                                                               H     H    2   OCH.sub.3                                   Q-10 (R.sub.8 = C.sub.2 H.sub.5)                                                                 H     H    1   CH.sub.3                                    Q-13 (R.sub.8 = SCH.sub.3)                                                                       H     H    1   OCH.sub.3                                   Q-10 (R.sub.8 = H) H     H    1   OC.sub.2 H.sub.5                            Q-10 (R.sub.8 = H) H     H    1   OCF.sub.2 H                                 Q-10 (R.sub.8 = SCH.sub.3)                                                                       H     H    2   CH.sub.3                                    Q-10 (R.sub.8 = CH.sub.3)                                                                        H     H    1   OCH.sub.3                                   Q-10 (R.sub.8 = H) H     H    1   CH.sub.3                                    Q-11 (R.sub.5 = H) H     H    1   CH.sub.3                                    Q-12 (R.sub.5 = CH.sub.3)                                                                        H     H    1   OCH.sub.3                                   Q-14 (R.sub.9 = Cl)                                                                              H     H    1   CH.sub.3                                    Q-20 (R.sub.5,R.sub.6 = H)                                                                       H     H    1   CH.sub.3                                    Q-20 (R.sub.5,R.sub.6 = H)                                                                       H     H    2   OCH.sub.3                                   Q-24 (R.sub.5,R.sub.6 = H)                                                                       H     H    1   OCH.sub.3                                   Q-48 (R.sub.5,R.sub.11,R.sub.12 = H)                                                             H     H    1   CH.sub.3                                    Q-10 (R.sub.8 = H) H     H    1   CH.sub.3                                    ______________________________________                                    

                  TABLE V                                                         ______________________________________                                         ##STR37##                                                                    Q             R     R.sub.1                                                                             n   X.sub.1                                                                              Y.sub.2                                                                            m.p. °C.                     ______________________________________                                        Q-1  (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-2  (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-3  (R.sub.5 = H)                                                                              H     H   1   CH.sub.3                                                                             H                                      Q-9  (R.sub.5,R.sub.6,R.sub.7 = H)                                                              H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-9  (R.sub.5,R.sub.6,R.sub.7 = H)                                                              H     H   2   OCH.sub.3                                                                            CH.sub.3                               Q-13 (R.sub.8 = SCH.sub.3)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-13 (R.sub.8 =  SCH.sub.3)                                                                     H     H   1   OCH.sub.3                                                                            CH.sub.3                               Q-10 (R.sub.8 = H)                                                                              H     H   1   OC.sub.2 H.sub.5                                                                     CH.sub.3                               Q-10 (R.sub.8 = CH.sub.3)                                                                       H     H   1   OCF.sub.2 H                                                                          CH.sub.3                               Q-10 (R.sub.8 = H)                                                                              H     H   1   CH.sub.3                                                                             H                                      Q-10 (R.sub.8 = H)                                                                              H     H   2   CH.sub.3                                                                             CH.sub.3                               Q-11 (R.sub.5 = H)                                                                              H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-12 (R.sub.5 = CH.sub.3)                                                                       H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-14 (R.sub.9 = Cl)                                                                             H     H   1   OCH.sub.3                                                                            CH.sub.3                               Q-20 (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-20 (R.sub.5,R.sub.6 = H)                                                                      H     H   2   OCH.sub.3                                                                            CH.sub.3                               Q-24 (R.sub.5,R.sub.6 = H)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-48 (R.sub.5,R.sub.11,R.sub.12 = H)                                                            H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-39 (R.sub.5 = H)                                                                              H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-39 (R.sub.5 =  CH.sub.3)                                                                      H     H   1   CH.sub.3                                                                             CH.sub.3                               Q-42 (R.sub.5 = H)                                                                              H     H   1   CH.sub.3                                                                             CH.sub.3                               ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations. broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE VI                                                        ______________________________________                                                    Active   Weight Percent*                                                      Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90     0-74      1-10                                        Oil Suspensions,                                                                            3-50      40-95     0-15                                        Emulsions, Solutions,                                                         (includingq Emulsifiable                                                      Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts         1-25      70-99     0-5                                         Granules and Pellets                                                                        0.1-95    5-99.9    0-15                                        High Strength 90-99     0-10      0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers"., 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates:solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 1477ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, March 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A Evans, "Weed control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 9 Wettable Powder

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:)80%

sodium alkylnaphthalenesulfonate: 2%

sodium ligninsulfonate: 2%

synthetic amorphous silica: 3%

kaolinite: 13%

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 10 Wettable Powder

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:50%

sodium alkylnaphthalenesulfonate: 2%

low viscosity methyl cellulose: 2%

diatomaceous earth: 46%

The ingredients are blended, coarsely hammermilled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 11 Granule

Wettable Powder of Example 10: 5%

attapulgite granules: (U.S.S. 20-40 mesh; 0.84-0.42 mm): 95%

A slurry of wettable powder containing 25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 12 Extruded Pellet

N[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:25%

anhydrous sodium sulfate: 10%

crude calcium ligninsulfonate: 5%

sodium alkylnaphthalenesulfonate: 1%

calcium/magnesium bentonite: 59%

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.Ser. No. 20 sieve (0.84 mm openings). The granules held on aU.S.Ser. No. 40 sieve (0.42 mm openings) may be packaged for use and thefines recycled.

EXAMPLE 13 Low Strength Granule

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:0.1%

attapulgite granules (U.S.S. 20-40 mesh): 99.9%

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 14 Granule

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:80%

wetting agent: 1%

crude ligninsulfonate salt (containing 5-20% of the natural sugars): 10%

attapulgite clay: 9%

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted tp gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 15 High Strength Concentrate

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:99%

silica aerogel: 0.5%

synthetic amorphous silica: 0.5%

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.Ser. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 16 Wettable Powder

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:90%

dioctyl sodium sulfosuccinate: 0.1%

synthetic fine silica: 9.9%

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.Ser. No. 50 screen and then packaged.

EXAMPLE 17 Wettable Powder

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:40%

sodium ligninsulfonate: 20%

montmorillonite clay: 40%

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 18 Low Strength Granule

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:1%

N,N-dimethylformamide: 9%

attapulgite granules (U.S.S 20-40 sieve:) 90%

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 19 Aqueous Suspension

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:40%

polyacrylic acid thickener: 0.3%

didecylphenol polyethylene glycol ether: 0.5%

disodium phosphate: 1%

monosodium phosphate: 0.5%

polyvinyl alcohol: 1.0%

water: 56.7%

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 20 Solution

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide,sodium salt: 5%

water: 95%

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for used.

EXAMPLE 21 Oil Suspension

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:35%

blend of polyalcohol carboxylic esters and oil soluble petroleumsulfonates: 6%

xylene: 59%

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 22 Dust

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide:10%

attapulgite: 10%

Pyrophyllite: 80%

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

Test results indicate that the compounds of the present invention arehighly active preemergent or postemergent herbicides or plant growthregulants. Many of them have utility for broad-spectrum pre-and/orpost-emergence weed control in areas where complete control of allvegetation is desired, such as around fuel storage tanks, ammunitiondepots, industrial storage areas, parking lots, drive-in theaters,around billboards, highway and railroad structures. Some of thecompounds have utility for selective weed control in crops such aswheat. Alternatively, the subject compounds are useful to modify plantgrowth.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as plant growthmodifiers or as herbicides, the crop species involved, the types ofweeds to be controlled, weather and climate, formulations selected, modeof application, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.05 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for selective weed control orfor situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide; examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.##STR38##

Test A

Seeds of crabgrass (Digitaria sp.), barnyard-grass Echinochloacrusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),velvetleaf (Abutilon theophrasti), cheatgrass (Bromus secalinus),morninglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum), sorghum,corn, soybean, sugarbeet, cotton, rice, wheat and purple nutsedge(Cyperus rotundus) tubers were planted and treated pre-emergence withthe test chemicals dissolved in a non-phytotoxic solvent. At the sametine, these crop and weed species were treated with a soil/foliageapplication. At the time of treatment, the plants ranged in height from2 to 18 cm. Treated plants and controls were maintained in a greenhousefor sixteen days, after which all species were compared to controls andvisually rated for response to treatment. The ratings, summarized inTable A, are based on a numerical scale extending from 0=no injury, to10=complete kill. The accompanying descriptive symbols have thefollowing meanings:

C=cholorosis/necrosis;

B=burn;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation;

X=axillary stimulation;

S=albinism; and

6Y=abscised buds or flowers.

                  TABLE A                                                         ______________________________________                                                  Cmpd. 1   Cmpd. 2   Cmpd. 3 Cmpd. 4                                 Rate kg/ha                                                                              .05       .05       .05     .05                                     POST- -EMERGENCE                                                              Morningglory                                                                            3H        2C,5G     2C      1H                                      Cocklebur 5C,9H     2C,9H     3G      1C                                      Velvet leaf                                                                             --        2G        0       0                                       Sicklepod 2C,3G     --        --      --                                      Nutsedge  5G        0         0       0                                       Crabgrass 0         0         0       0                                       Barnyardgrass                                                                           3C,9H     3C,8H     2C,8H   2C,5H                                   Cheatgrass                                                                              2C,6G     2C,8G     0       4G                                      Wild Oats 0         0         0       0                                       Wheat     0         0         0       0                                       Corn      4C,9H     3H        0       0                                       Soybean   5C,9G     4C,9G     1H      2C,7G                                   Rice      8G        2H        4G      5G                                      Sorghum   3C,8H     2C,4G     2C      2C,5G                                   Sugar beet                                                                              9C        5C,9H     4G      3C,3H                                   Cotton    4C,8H     4C,5G     0       0                                       PRE-                                                                          EMERGENCE                                                                     Morningglory                                                                            10E       6H        0       0                                       Cocklebur 3H        1C        0       0                                       Velvet leaf                                                                             --        0         0       0                                       Sicklepod 0         --        --      --                                      Nutsedge  0         0         0       0                                       Crabgrass 0         0         0       0                                       Barnyardgrass                                                                           2C        0         0       0                                       Wild Oats 0         0         0       0                                       Wheat     0         0         0       0                                       Corn      3C,8H     2G        1C      0                                       Soybean   2C,2H     3G        0       0                                       Rice      4C,8G     2G        5G      0                                       Sorghum   3C,8H     2C,4G     2C,5G   0                                       Sugar beet                                                                              5G        3C,4G     0       0                                       Cotton    6G        2C        0       0                                       Cheatgrass                                                                              4C,8G     0         0       0                                           Cmpd. 5             Cmpd. 6   Cmpd. 7                                     Rate kg/ha                                                                        .05                 .05       .05                                         POST-EMERGENCE                                                                Morningglory                                                                      2C                  2C        3C,6G                                       Cocklebur                                                                         1C                  2G        5C,9G                                       Velvet leaf                                                                       0                   1C        10C                                         Sicklepod                                                                         --                  --        --                                          Nutsedge                                                                          0                   0         4C,9G                                       Crabgrass                                                                         0                   0         3G                                          Barnyardgrass                                                                     0                   0         3C,8H                                       Cheatgrass                                                                        0                   0         2C,8G                                       Wild Oats                                                                         0                   0         0                                           Wheat                                                                             0                   0         0                                           Corn                                                                              0                   0         3H                                          Soybean                                                                           0                   1H        4C,9G                                       Rice                                                                              0                   0         3G                                          Sorghum                                                                           0                   0         2C,9H                                       Sugar beet                                                                        2C,7H               3H        9C                                          Cotton                                                                            1C                  0         4C,8G                                       PRE-EMERGENCE                                                                 Morningglory                                                                      0                   0         5G                                          Cocklebur                                                                         0                   0         0                                           Velvet leaf                                                                       0                   0         5G                                          Sicklepod                                                                         --                  --        --                                          Nutsedge                                                                          0                   0         4G                                          Crabgrass                                                                         6G                  0         0                                           Barnyardgrass                                                                     0                   0         3G                                          Cheatgrass                                                                        0                   0         0                                           Wild Oats                                                                         0                   0         2G                                          Wheat                                                                             0                   0         2G                                          Corn                                                                              0                   0         5G                                          Soybean                                                                           0                   0         2G                                          Rice                                                                              0                   0         0                                           Sorghum                                                                           0                   0         2G                                          Sugar beet                                                                        0                   0         5G                                          Cotton                                                                            0                   0         2G                                          ______________________________________                                    

What is claimed is:
 1. Compounds of the formula: ##STR39## wherein R isH or CH₃ ;R₁ is H, F, Cl, Br, Ch₃, CF₃, OCH₃, SCH₃, OCHF₂ and SCHF₂ ; nis 1 or 2; ##STR40## R₅, R₆, R₇ and R₁₀ are independently H or CH₃ ; R₈is H, CH₃, CH₂ CH₃, SH, SCH₃, SCH₂ CH₃, OCH₃, OCH₂ CH₃, SCF₂ H, SCH₂CH═CH₂ or SCH₂ CN; R₉ is H or Cl; R₁₁ and R₁₂ are independently H, CH₃or OCH₃ ; and R₁₃ and R₁₄ are independently CH₃ or OCH₃ ; ##STR41## X isCH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, I, OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂,OCH₂ CF₃ or CF₃ ; Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃,N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂OCH₂ CH₃, ##STR42## or cyclopropyl; m is 2 or 3; L₁ and L₂ areindependently O or S; R₂ is H or CH₃ ; R₃ and R₄ are independently C₁-C₂ alkyl; Z is CH;provided that (a) when X is Cl, F, Br or I, then Y isOCH₃, OC₂ H₅, N(OCH₃)CH₃, NHCH₃, N (CH₃)₂ or OF₂ H; (b) when Q is Q-1,Q-2, Q-4, Q-5, Q-6, Q-8Q-23, Q-24, Q-25, Q-26, Q-27, Q-28, Q-29, Q-45,Q-46, Q-47, Q-51 or Q-52, then one of R₅ or R₆ is other than H; (c) whenQ is Q-10 or Q-13, then R₈ is other than H, CH₃ or CH₂ CH₃ ; (d) when Qis Q-14, then R₉ is other than H; (e) when Q is Q-3, Q-18 or Q-19, thenR₅ is CH₃ ; (f) when Q is Q-31 or Q-33, then one of R₅, R₆ or R₇ isother than H; (g) when Q is Q-48, then one of R₅, R₁₁ or R₁₂ is otherthan H; (h) when Q is Q-49 or Q-50, then one of R₁₁ or R₁₂ is other thanH; (i) when Q is Q-53 or Q-54, then one of R₁₃ and R₁₄ is other than H;and their agriculturally suitable salts.
 2. Compounds of claim 1 whereinR is H.
 3. Compounds of claim 2 wherein Q is Q-1, Q-2, q-3, Q-6, Q-7,Q-8, QA-9, Q-10, Q-13, Q-14, Q-17, Q-20, Q-23, Q-24, Q-25, Q-26, Q-29,Q-30Q-31, Q-32, Q-33, Q-34, Q-35, Q-36, Q-37, Q-38, Q-40, Q-41, Q-43,Q-44, Q-45, Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, Q-54 4.Compounds of claim 3 wherein Y is CH₃, OCJ₃, CH₂ OCH₃, NHCH₃, CH₂ CH₃,CH(OCH₃)₂, or cyclopropyl.
 5. Compounds of claim 4 wherein R₁ is H, Cl,CH₃, SCH₃, or OCH₃ and X is CH₃, OCH₃, Cl, Br, or OCF₂ H.
 6. Compoundsof claim 5 wherein n is
 2. 7. Compounds of claim 5 wherein Q is Q-1,Q-2, or Q-3.
 8. Compounds of claim 5 wherein Q is Q-6, Q-7, Q-8, or Q-9.9. Compounds of claim 5 wherein Q is Q-10.
 10. Compounds of claim 5wherein Q is Q-13, Q-14, Q-17, or Q-20.
 11. Compounds of claim 5 whereinQ is Q-23, Q-24, Q-25, Q-26, Q-29, or Q-30.
 12. Compounds of claim 5wherein Q is Q-31Q-32, Q-33, or Q-34.
 13. Compounds of claim 5 wherein Qis Q-35, Q-36, Q-37, or Q-38.
 14. Compounds of claim 5 wherein Q isQ-40, Q-41, Q-43, or Q-44.
 15. Compounds of claim 5 wherein Q is Q-45,Q-46, Q-47, Q-48, Q-49, Q-50, Q-51, Q-52, Q-53, or Q-54.
 16. Thecompound of claim 1 which is N-8(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-(5-methylthio-1,3,4-thiadiazol-2-ylmethyl)benzenesulfonamide.17. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant, solid or liquid diluent.18. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 2and at least one of the following: surfactant, solid or liquid diluent.19. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 3and at least one of the following: surfactant, solid or liquid diluent.20. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 4and at least one of the following: surfactant, solid or liquid diluent.21. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid or liquid diluent.22. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 6and at least one of the following: surfactant, solid or liquid diluent.23. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 7and at least one of the following: surfactant, solid or liquid diluent.24. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 8and at least one of the following: surfactant, solid or liquid diluent.25. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 9and at least one of the following: surfactant, solid or liquid diluent.26. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 10and at least one of the following: surfactant, solid or liquid diluent.27. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 11and at least one of the following: surfactant, solid or liquid diluent.28. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 12and at least one of the following: surfactant, solid or liquid diluent.29. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 13and at least one of the following: surfactant, solid or liquid diluent.30. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 14and at least one of the following: surfactant, solid or liquid diluent.31. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 15and at least one of the following: surfactant, solid or liquid diluent.32. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 16and at least one of the following: surfactant, solid or liquid diluent.33. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 34. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 35. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 36. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 37. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 5. 38. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim6.
 39. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 7. 40. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 8. 41. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim9.
 42. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 10. 43. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 11. 44. A methodfor controlling the growth of undesired vegetation which comprisesapplying to the locus to be protected an effective amount of a compoundof claim
 12. 45. A method for controlling the growth of undesiredvegetation which comprises applying to the locus to be protected aneffective amount of a compound of claim
 13. 46. A method for controllingthe growth of undesired vegetation which comprises applying to the locusto be protected an effective amount of a compound of claim
 14. 47. Amethod for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 15. 48. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 16. 49. Compoundsof the formula: ##STR43## wherein R is H or CH₃ ;R₁ is H, F, Cl, Br,Ch₃, CF₃, OCH₃, SCH₃, OCHF₂ or SCHF₂ ; n is 1 or 2; Q is ##STR44## R₅,R₆, R₇ and R₁₀ are independently H or CH₃ ; R₈ is H, CH₃, CH₂ CH₃, SCH₃,SCH₂ CH₃, OCH₃, OCH₂ CH₃, SCF₂ H, SCH₂ CH═CH₂ or SCH₂ CN; R₉ l is H orCl; R₁₁ and R₁₂ are independently H, CH₃ or OCH₃ ; and R₁₃ and R₁₄ areindependently CH₃ or OCH₃ ; ##STR45## X is CH₃, OCH₃, OCH₂ CH₃, Cl, F,BR, I, OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃ or CF₃ ; Y is H,CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃,SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, ##STR46## m is 2 or 3;L₁ and L₂ are independently O or S; R₂ is H or CH₃ ; R₃ and R₄ areindependently C₁ -C₂ alkyl; Z is CH.provided that (a) when X is Cl, F,Br or I, then Y is OCH₃, OC₂ H₅, N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂ H;(b) when Q is Q-1, Q-2, Q-4, Q-5, Q-6, Q-8, Q-23, Q-24, Q-25, Q-26,Q-27, Q-28, Q-29, Q-45, Q-46, Q-47, Q-51 or Q-52, then one of R₅ or R₆is other than H; (c) when Q is Q-10, then R₈ is other than H, CH₃ or CH₂CH₃ ; (d) when Q is Q-14, then R₉ is other than H; (e) when Q is Q-3, orQ-19, then R₅ is CH₃ ; (f) when Q is Q-31 or Q-33, then one of R₅, R₆ orR₇ is other than H; (g) when q is Q-48, then one of R₅, R₁₁ or R₁₂ isother than H; (h) when Q is Q-49 or Q-50, then one of R₁₁ or R₁₂ isother than H; (i) when Q is Q-53 or Q-54, then one of R₁₃ and R₁₄ isother than H;and their agriculturally suitable salts.
 50. Compounds ofthe formula: ##STR47## wherein R is H or CH₃ ;R₁ is H, F, Cl, Br, CH₃,CF₃, OCH₃, SCH₃, OCHF₂ or SCHF₂ ; n is 1 or 2; ##STR48## X is CH₃, OCH₃,OCH₂ CH₃, Cl, F, Br, I, OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃or CF₃ ; Y is H, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃,N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃,##STR49## or cyclopropyl; m is 2 or 3; L₁ and L₂ are independently O orS; R₂ is H or CH₃ ; R₃ and R₄ are independently C₁ -C₂ alkyl; Z is CH:provided that when X is Cl, F, Br, or I, then Y is OCH₃, OC₂ H₅,N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂ H; and their agriculturally suitablesalts.
 51. Compounds of the formula: ##STR50## wherein R is H or CH₃ ;R₁is H, F, Cl, Br, CH₃, CF₃, OCH₃, SCH₃, OCHF₂ or SCHF₂ ; n is 1 or 2; Qis ##STR51## R₈ is SH, SCH₃, SCH₁₂ CH₃, OCH₃, OCH₂ CH₃, SCF₂ H, SCH₂CH═CH₂ or SCH₂ CN; ##STR52## X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, I,OCF₂ H, CH₂ F, OCH₂ CH₂ F, OCH₂ CHF₂, OCH₂ CF₃ or CF₃ ; Y is H, CH₃,OCH₃, OC₂ H₅, CH₂ OCH₃, NHCH₃, N(OCH₃)CH₃, N(CH₃)₂, CH₂ CH₃, CF₃, Sch₃,OCH₂ CH═CH₂, OCH₂ C.tbd.CH, CH₂ OCH₂ CH₃, ##STR53## or cyclopropyl; m is2 or 3; L₁ and L₂ are independently O or S; R₂ is H or CH₃ ; R₃ and R₄are independently C₁ -C₂ alkyl; Z is CH; provided that when X is Cl, F,Br or I, then Y is OCH₃, OC₂ H₅, N(OCH₃)CH₃, NHCH₃, N(CH₃)₂ or OCF₂H;and their agriculturally suitable salts.
 52. Compounds of claim 49wherein Q is Q-9, Q-20, Q-22, Q-30, Q-35, Q-36, Q-37, Q-38, Q-39, Q-40,Q-41, Q-42, Q-43 or Q-44.
 53. Compounds of claim 49 wherein R₈ is SCH₃,SCH₂ CH₃, OCH₃, OCH₂ CH₃, SCF₂ H, SCH₂ CH═CH₂ or SCH₂ CN.
 54. Compoundsof claim 49 wherein Q is Q-7, Q-17, Q-18, or Q-32.